You'll be going during the fall, which is a lot milder than the fall season in Chicago. It does rain sometimes though, so be prepared clothing wise... I'd get an elementary "Italian for Travelers" type book, and try to get somewhat comfortable with counting, asking for basic items, etc.
You'll be going to a region with a lot of places to see including Napoli itself, Vesuvio, Herculanum, Pompeii, the Phlegrean Fields, Capri, ......... It would be hard to give recommendations as there's so much to see and do, but this site (available in English) can help you decide what you'd like to see and do.
http://www.dentronapoli.it/ This will keep you busy at least for a few weeks!
For major excursions, you can rely on your hotel to offer them in their package deals. If you're a bit adventurous, you might want to purchase a map of Naples as soon as you're in the city. (Any newspaper stand will carry them). A lot of places you can find yourself; you'll save money, and you'll get to intermingle with the Napolitani, which should be part of any vacation experience. The Napolitani are very gregarious, but have a reputation for fleecing tourists, so you have a caveat to remember. You'll find Italians to be really nice people, and are very helpful with tourists, even if you don't speak the language. Again, walk around the city, and get a bit of the sights, sounds and flavors of the city. There are more churches than McDonalds here too, so if you like to see them, they're waiting your perusal...
Also, beware of pickpockets! Get you and the Mrs. those neck carry document holders which carry cash, etc., and are worn under your shirt. Keep your passport in the hotel's safe, and carry a photocopy with you with the phone numbers of your hotel, local police, etc., etc. Bring American Express Traveler's Checks, and carry them and small amounts of cash. Leave your Patek Philippe and bling bling jewelry at home!
If you're really adventurous (read REALLY), rent a car, and get the AAA International Driver's License before you leave. Driving rules are forgotten once you are within Naple's city limits, as in most other places here too! It is great to have a sports car here though!
If you are pulled over, Italian police are very nice, and will not come across like their New Jersey Highway Patrol cousins!
Be careful too while on foot in the city; try crossing the white lined pedestrian crossings!!!
Pizza was invented in Naples, so ask the locals where the best pizza is to be found. Order the Margherita, which is pizza with mozzarella and tomato sauce. Naples make the best mozzarella around, so also order a Caprese with one of your meals, which is a salad consisting of alternating slices of tomatos, and Mozzarella made from buffalo milk, with salt, pepper, and parsley. You can order buffalo mozzarella pizzas, but the cheese it a bit watery, so many prefer the normal cow's milk mozzarella. While we're talking of food, the seafood in Naples borders on the spectacular. A plate of Spaghetti with "Frutta di Mare" (fruit of the sea [mixed seafood]) is incredible! The wines are also excellent, and you can ask while there which ones to try.
If you get bored in the part of Italy in which you'll be visiting, Rome is only 2 hours away by train, and will keep you occupied for any remaining portion of your trip!
Have never received feedback from tourists who did not enjoy Italy, so I'm sure you will have a great time. Personal tip-- Do NOT walk around with any of H.I.'s products in hand... If you'd like any specific advice or additional help, post here, or send me an e-mail!
Buon Viaggio!
